When New York City police officer O'Malley learns of a young man who is about to embark on a life of crime by taking part in a robbery, he takes the boy aside and tells him the story of Boomerang Bill, another wanna-be gangster who wanted to be a big shot in the New York crime scene. It seems that Bill fell for a pretty young dance-hall girl, and went up against local gang boss Tony the Wop when he insulted her. Tony, who never forgot a slight, found a way to make things very, very tough for Boomerang Bill, in a way that he never saw coming.

Notorious pirate Joaquin Santos lives by the saying, "Dead Men Tell No Tales". He conspires with the prominent Squire Rattray to take over and plunder the Lady Jermyn, a ship carrying a considerable amount of gold, and then destroy the ship and kill its crew. Rattray, who is in love with Santos' daughter Eve, agrees to pick up the pirate, his crew and their loot on his private yacht after the deed is done. However, young George Cole, a passenger on the Lady Jermyn who is also in love with Eve, survives the attack and sets out to find her.